N1-α-Naphthyl-2-[(2-methyl-1H-3-indolyl)acetyl]-1-hydrazinecarbothioamide | 211562-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N1-α-Naphthyl-2-[(2-methyl-1H-3-indolyl)acetyl]-1-hydrazinecarbothioamide
• CAS: 211562-08-2
• 化学式: C₂₂H₂₀N₄OS
• 分子量: 388.493
• InChiKey: HEWKBENOQQBIEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  68.95
• 氢给体数：
  4.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N1-α-Naphthyl-2-[(2-methyl-1H-3-indolyl)acetyl]-1-hydrazinecarbothioamide 在 硫酸 作用下， 反应 0.17h， 以88%的产率得到5-[(2-methyl-1H-indol-3-yl)methyl]-N-naphthalen-1-yl-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2,4-triazole

  摘要：

  3-[ (2-Methyl-1H-3-indolyl)methyl]-4-aryl-4, 5-dihydro-1H-1,2,4-triazole-5-thiones 6a-c and their respective N-{5-[ (2-methyl-1H-3-indolyl) methyl] -1,3,4-thiadiazol-2-yl}-N-arylamines 7a,b have been prepared. The antidepressant profile of 6a,c and 7a was studied on mice with respect to that of the analogous 3-(1H-1-indolylmethyl)-4-aryl-4,5-dihydro-1H-1,2,4-triazole-5-thiones 1a-c and the respective N-{5-[ (2-methyl-1H-3-indolyl) methyl ]-1,3,4-thiadiazol-2-yl}-N-arylamines 2a-c, the synthesis and antimicrobial potency of which we have recently reported. Behavioral effects, induced by the members of both series,in conjunction with their activity in some specific tests (forced swim, pentetrazole convulsions) on mice, show that these derivatives cross the blood-brain barrier and could develop an antidepressant activity comparable to that of imipramine. Blood-brain barrier penetration is also supported by the lipophilicity data obtained for all analogs. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00024-x
• 作为产物：
  描述：

  2-甲基吲哚-3-乙酸 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 N1-α-Naphthyl-2-[(2-methyl-1H-3-indolyl)acetyl]-1-hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2,4-triazole

  摘要：

  3-[ (2-Methyl-1H-3-indolyl)methyl]-4-aryl-4, 5-dihydro-1H-1,2,4-triazole-5-thiones 6a-c and their respective N-{5-[ (2-methyl-1H-3-indolyl) methyl] -1,3,4-thiadiazol-2-yl}-N-arylamines 7a,b have been prepared. The antidepressant profile of 6a,c and 7a was studied on mice with respect to that of the analogous 3-(1H-1-indolylmethyl)-4-aryl-4,5-dihydro-1H-1,2,4-triazole-5-thiones 1a-c and the respective N-{5-[ (2-methyl-1H-3-indolyl) methyl ]-1,3,4-thiadiazol-2-yl}-N-arylamines 2a-c, the synthesis and antimicrobial potency of which we have recently reported. Behavioral effects, induced by the members of both series,in conjunction with their activity in some specific tests (forced swim, pentetrazole convulsions) on mice, show that these derivatives cross the blood-brain barrier and could develop an antidepressant activity comparable to that of imipramine. Blood-brain barrier penetration is also supported by the lipophilicity data obtained for all analogs. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00024-x